(Diethylamino)sulfur trifluoride → HCID 131736490, compound

HRID 1477610Notes

Reaction equation

HRID 1477610 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:9]1[C@H:13](O)[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:35])CC)C>ClCCl>[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:9]1[C@H:13]([F:35])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 131736489HCID 131736489, compound

Product 1

HCID 131736490HCID 131736490, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (8.7 mL) of tert-butyl (3R,4R)-3-(dibenzylamino)-4-hydroxypyrrolidine-1-carboxylate (320 mg, 0.92 mmol) synthesized in Reference Synthesis Example 71, (diethylamino)sulfur trifluoride (295 mg, 1.84 mmol) was added at 0° C. and the resultant solution was stirred at room temperature. After completion of the reaction, the reaction solution was washed with water and saturated sodium bicarbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product (240 mg) of the title compound. The crude product was used in the next reaction as it was.

Workup

  1. additionwas added at 0° C.
  2. customAfter completion of the reaction
  3. washthe reaction solution was washed with water and saturated sodium bicarbonate aqueous solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d75015c74b6e419f9e14ebbbb680f14d
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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